1-(2,2-Dimethyl-propionyl)-3-{2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl}-1H-thieno[3,4-d]pyrimidine-2,4-dione | 123213-68-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,2-Dimethyl-propionyl)-3-{2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl}-1H-thieno[3,4-d]pyrimidine-2,4-dione
• 英文别名: 1-(2,2-Dimethylpropanoyl)-3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]thieno[3,4-d]pyrimidine-2,4-dione
• CAS: 123213-68-3
• 化学式: C₂₅H₂₈FN₃O₄S
• 分子量: 485.579
• InChiKey: VTRRZDFRSVKCJP-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  627.8±65.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(3-{2-[4-(4-Fluoro-benzoyl)-piperidin-1-yl]-ethyl}-ureido)-thiophene-3-carboxylic acid methyl ester 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 1-(2,2-Dimethyl-propionyl)-3-{2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl}-1H-thieno[3,4-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Thiophene systems. 12. Analogues of ketanserin and ritanserin as selective 5-HT2 antagonists

  摘要：

  A series of thieno[3,2-d]-, [3,4-d]- and [2,3-d]pyrimidinedione derivatives was prepared with N-3 substitution containing the side chains of ketanserin and ritanserin. The best of these thiophene analogues were the isosteres of ketanserin which were up to 20-fold more potent than the standards in 5-HT2 binding assays. More importantly, in addition to their increased potency, these derivatives were more selective than the standards in that they had less affinity for 5-HT1A and alpha-1 binding sites. This selectivity is especially noted as the ratio of alpha-1/5-HT2 wherein the most interesting thiophene isostere (2) in this study had a binding selectivity > 12-fold of ketanserin or ritanserin.

  DOI：

  10.1016/0223-5234(91)90007-a